My First Time

One of the most important things that have ever happened in my life was the first time I was ever with a guy in a situation other than just friends. It is probably one of the most difficult things to deal with when you realize that your sexuality is something other than the “status quo”, something a little out of the ordinary and, in my case, my feelings of bisexuality.

For the longest time I struggled with my feelings, only really discussing them with strangers on the Internet. At that time, I split up with my then girlfriend and moved in temporarily when an old friend of mine, David. We had been friends for a long time and I had always known that he was a cross-dresser, but he had never displayed any doubts that he was anything other than straight.

So, I moved into his apartment and everything was ok, life continued pretty much as normal. Then, about 3 days later, an old friend of ours, Sam, came around to visit us when she realized that I had moved in. Both myself and David had a history with Sam, and I knew that David secretly wanted to be back with her. Sam was a beautiful girl, about 5 feet 10 tall, with long flowing blonde hair, deep blue eyes, and wearing a long red velvet dress accentuating her beautiful 34d breasts, the low cut leaving her cleavage showing perfectly.

Myself, David and Sam did what we had done for a long time, sitting around and listening to music, having a couple of beers and bullshitting. After a couple of beers, we were feeling kinda loose and the talk got onto piercings and tattoos. At the time I had my lip, eyebrow and tongue (which I still have) pierced, and I knew Sam had her tongue pierced. What I didn’t know is that she had recently had her nipples pierced, and of course as soon as she said this, we were pushing her to show us. It didn’t take us long to persuade, and she stood, turning back to us slowly and lowering the straps of her dress till her gorgeous breasts were exposed, and her pierced nipples were in front of us, one with a purple ring and the other with a red ring. You could feel the electricity in the room, as both David and I stared at Sam. She smiled at us, and beckoned for us to stand up, which we both did, standing either side of her, and feeling a nipple each, and I bent down, taking the ring on her left nipple into my mouth, playing with it with my tongue, as David did the same with her right breast. Sam moaned slightly, leaning back on the window sill to steady herself.

After a few moments, Sam suggested we go into the bedroom, and we all did, sitting on the bed with Sam between us. We each kissed Sam in turn, then Sam told me to lie down, which I did without hesitation, stripping off my top as I did so. Sam stood up once again, slipping off her dress completely and showing her red lace panties to us, smiling as she did so and beckoning for us to strip completely. It didn’t take us long to do, and as myself and David took off our underwear, I had to stop myself from gasping at the size of David’s cock. Now, I am quite happy at myself, my cock being about 7 inches long and reasonably thick, but David’s was huge, easily 9 inches and very thick. I looked at Sam, who knew about me being bi as she was also bi, and smiled, then led down as she had instructed.

Sam came over to the bed, sitting next to me, her hand stroking my leg then over, playing with my hard cock as she looked at David as he stroked his cock, then she moved forward, kissing me again, passionately, our tongues playing with each others, as I played with her nipples in turn.

It was then that the biggest surprise of my life happened, as I felt a mouth around the head of my cock, fumbling with it awkwardly as if it was the first time the mouth had ever done this. I looked down, and realized with a shocked look that David was sucking my cock. I gasped, enjoying the sensations, then David stopped, and sat back again, stroking his cock slowly, and I knew I wanted his cock in my mouth. I knelt up and leaned over, looking into his eyes then at Sam, who nodded for me to go ahead, and I leaned over and licked the tip, tasting my first ever cock, enjoying the sensations.

Unfortunately, that was as far as it went as Sam had to leave, and David, embarrassed I think at what had happened, left for a while, and I was left wishing that we could have gone further, but knew that I would have to be patient. As it turned out, I didn’t have to wait long till I got my chance.

A couple of weeks later, I had been out for a few drinks and made my way home at around midnight, a little drunk but not overly so. As I walked in, David greeted me from the living room and I replied, going into my room to lie down and let my head settle a little. David came in a few minutes later, and we chatted for a while about nothing in particular, and somehow the conversation got around to my bisexuality, David questioning about if I had been with anyone and who I wanted to be with. I told him that I had not been with any guy, apart from what happened the other day with us and Sam, and David looked surprised.

What I said next surprised him even more, and to this day I don’t know where I got the bravado to say it from. I told him that I wanted him to be the first guy I was properly with. He look stunned, turning a bright red, and I felt awful, realizing I had embarrassed him.

“I’m not into guys,” he replied suddenly, and not utter convincingly. I nodded understandingly, not wanting to alienate him at all, and simply replied, “well, if that ever changes, you know ok?”. David didn’t say anymore, and left a minute or so later, leaving the door open and the light on. I was feeling very horny by this time, my mind on the conversation, and I stripped down, covering myself with a light blanket and started to stroke my cock. It wasn’t long before I was led with my eyes closed, the covers pushed off me and wanking my cock faster, enjoying the sensations.

Suddenly, I sensed that someone was at the door watching, but I continued for a while longer, until David spoke softly, apologizing for disturbing me. I opened my eyes, saying it was ok, and that I should have shut the door, and he left, switching off the light as he did so but leaving the door open, and I sighed, feeling that the chance I may have had had now gone. I stopped, and led looking at the ceiling, trying to calm myself down.

A couple of minutes later I heard the door to David’s room opened, and I turned on my side, looking towards my door and wondering what he was doing. In the dimness, I suddenly saw him at the entrance to my room, and I immediately wondered what was happening.

“I changed my mind,” he simply said, so I told him to come over to me. He stood right next to my bed, and I could see that he was wearing no top, a pair of tights and a suspender belt – it was always a joke between us that he had the legs for wearing them despite being a guy! - and his hard cock sticking out in front of him.

I didn’t hesitate in taking his cock in my hand, stroking it lightly, then I leant forward and flicked my tongue over the end of his cock, enjoying the full taste for the first time. It was a great feeling to be doing what I had wanted to do, as I licked the head of his cock. He pushed me back, sitting over my face, and for the first time I took a cock into my mouth, starting with just the tip, licking and sucking on it softly at first. David moaned as I did so, his hands holding himself up on the wall.
I sucked on the head of his cock more, greedily lapping at it, then I took all of his cock in his mouth, surprised that I could get all of his large dick in my mouth. I continued to suck on it, taking his shaft in and out of my mouth, and licking up and down it. As I did so, I stroked my own cock, amazed that I was finally in this position, sucking on his cock noisily as he moaned at the sensations he was feeling from my mouth.

After a few minutes, David grabbed the back of my head, pushing his cock to the back of my throat, and I sucked on him harder, realizing that he was close to cumming. As he bucked against me, he grabbed his cock, stroking it in my face, faster and harder all the time till he came over my face, his cum spurting on my cheek and down over my chest, and I tasted someone’s cum for the first time, licking it off my fingers and enjoying the salty taste. As I did so, I came too, spurting my cum over my chest, and I gasped, my body shivering from the sensations.

It was the most amazing thing that has happened to me, and although me and David did do stuff a couple of times more in the week or so after, the situation changed so it didn’t happen after that, which is such a shame. Its something I’m dying to try again, and hopefully someday very soon...